Creative Tax Deductions

It's about that time again. Yes, it's time to see your accountant to see what he or she can do to lower that pesky tax bill of yours. From wedding costs to private planes to car wrecks, here are some of the most creative tax deductions ever attempted. Don't try this at home, folks.

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A Massachusetts CPA tells the hilarious tale of a man who wanted to deduct the cost of his wedding. As his perplexed accountant put it, "I could not understand where he expected to record it. As a charitable donation? Like he was nice enough to marry her?"

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Another Massachusetts CPA tells of a state trooper who tried to deduct the cost of his haircuts. He thought they were deductible because he had to keep his hair short for work. He was wrong.

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A New Jersey woman tried to deduct the cost of her home security system. After all, she rationalized that she wouldn't be able to pay taxes if she got killed in a break-in. Creative, but ultimately unsuccessful.

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Another gem from Massachusetts: A self-employed businessman took enormous liberties with the "dues and subscriptions" deduction by attempting to write off thousands in adult magazine subscriptions. The accountant persuaded him to include them as "nondeductible personal expenses" on his return.

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Now this is creative: In 2011, a man actually tried to pass off a former spouse as a dependent. Apparently, this is legal, as long as you don't try to claim said ex during the year you divorce.

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Generally speaking, swimming pools aren't tax deductible. But one man convinced his accountant that he needed it for medical reasons. How? Well, the man did suffer from emphysema and had developed an exercise routine with his doctor to help his breathing.

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A man had too much to drink at a party and decided not to drive home -- only to change his mind a few hours later. He ran his car off the road and was arrested for drunk driving, and his insurance company refused to pay for the damage to his car. Amazingly, the (somewhat) responsible reveler managed to get the Tax Court to deduct the cost of the damage because he tried to do the right thing by not driving home right away.

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How's this for a business expense? A service-station owner was able to deduct the free beer he gave away instead of trading stamps. Apparently, the IRS just sees that as the cost of doing business.

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The Minnesota Society of CPAs offers the tale of a creative taxpayer who wanted to deduct the market value of the blood he'd donated over the past year. We know blood is valuable, but this is ridiculous.

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How bad was your marriage if you try to write off your attorney's fees for your divorce?

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Breast implants usually can't be deducted for tax purposes, but in 1994, a Tax Court allowed an exotic dancer to deduct more than $2,000 for her implants. Their extreme size (56FF) made it clear that they were just for business purposes.

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In 2001, a Tax Court approved a cat food deduction for a South Carolina couple who set the food out for the cats. Why? The kitties would chase away critters who would otherwise overrun their scrap yard. Awww!

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When the IRS disallowed Cory Wheir's deduction for bodybuilding oils in 2004, the part-time bodybuilder sued -- and won. The Tax Court allowed the oils, but nixed the 3 pounds (1.36 kilograms)of bison meat he also deducted. After all, most bodybuilders don't eat bison ... right?

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Ah, the trials of the 1 percent: A couple decided to forgo the long drive to their rental property, so they solved the problem by buying their own plane. Amazingly, the Tax Court allowed the couple to deduct the cost of the trips, including fuel costs.

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Did you know that you could write off a business trip to Bermuda without having to explain why you have any business in the country? It's true, thanks to an agreement to a tax information exchange agreement between Bermuda and the U.S. Have fun!